Method of producing mercaptans of the furfuryl series



Patented Feb. 25, 1930 UNITED STATES IPA-TENT OFFICE STAUDINGER, F FREIBURG, GERMANY, AND THADEUS REICHSTEIN, OF ZURICH, SWITZERLAND, ASSIGNORS TO FIRM INGA INTERNATIONALE NAHBUNGS- UND GENUSSMITTEL AKTIENGESELLSCHAFT, OF- SCHAFFHAUSEN, GERMANY METH OD OF TBODUGING MERCAPTANS OF THE FURFUIR-YL SERIES ll'o Drawing. Original application filed July 22, 1927, Serial No. 207,814, and in Germany December 16,

1926. Divided and this application filed June 9, 1928. Serial No. 284,274.

The present-invention relates to the production of mercaptans of the furfuryl series and is adivision of application Ser. No.

207 ,814, filed July 22. 1927, Patent No. f

1,715,795, dated June 4, 1929.

The subject matter of the present invention is a method of producing a-hydroxy-methylfurfuryl-mercaptan and the novel product obtained. A

The a-hydroxy-methyl-furfuryl-mercaptan of the formula may be produced from the corresponding disulphide by reduction or directlyfrom the corresponding furfural by converting the latter by means of an alkaline sulphide compound for instance ammonium-sulph-hy- 2o drate, NH SH or sodium-sulph-hy'drate NaSI-I, into the disulphide and reducing the latter without isolating it to mercaptan.

Example 1 a-hydroxymethyl furf uryl disulphide, a

Example 2 trated alcoholic solution ammonium=sulphhydrate is added, thereby a reaction starts causing a rise of temperature and this reaction is terminated by introducing sulphide of hydrogen. After standing for approximately a day the bulk of a-hydroxymethyl-disulphide crystallizes. The latter is filtered and without cohol and reduced with activated aluminium (amalgamated aluminum powder). The re- T0 a-hydroxymethyl-furfurol in a concen-,

duction may also be carried out in a solution of ether, however, suflicient solvent must be added as the disulphide is reluctantly soluble in ether.-

We claim: 1

1. The herein described product consisting of a -'hydroxy methyl furfuryl-mercaptan,

the sailiebeing a viscid oil having a boiling point of about 106 C. at 2 G. at 0.5 mm. mercury and possessing a peculiar unpleasant mercaptan odour.

2. The process of producing a-hydroxymethyl-furfuryl-mercaptan, which consists in subjecting a-hydroxy-methyl-furfuryl-disulfideto the action of a reducing a cut.

3. The process of producing aydroxymethyl-furfuryl mercaptan, which consists in converting a-hydroxy-methy-l-furfuryl into a-hydroxy-methyhfurfuryl-disulfide by causing it to react with an alkaline sulphide compound, and subjecting the disulphide obtained, without isolating it, to thev action of a reducing agent.

4. The process of producing -hydroxymethyl-furfuryl-mercaptan, whlch consists in converting a-hydroxy-methyhfurfural into a hydroxy methyl furfuryl-disulphide by causing it to react with a soluble salt of hydrogen sulphide, and subjecting the disulphide obtained, .without isolating it, to the actionof a reducing agent.

5. The process of producing a-hydroxymethyl-furfuryl-mercaptan, which consists in converting a-hydroxy-methyl-furfural into a hydroxy methyl furfuryl-disulphide by causing it to react with ammonium-sulphohydrate and terminating the reaction by introducing sulphide of hydrogen, and subj ecting the disulphide obtained, .without isolat- "ing it, to the reducing action of activated aluminium.

In testimony that we claim the foregoing as our invention, we have signed our names. HERMANN STAUDINGER, PH. D.- THADEUS REICHSTEIN, PH. D.

further purifying is absorbed in al- 

